1. Match the compound with the C-NMR spectra. The chemical shifts are the values in ppm.

Compounds:

1. (CH3)2-C=CHCH2CH2CHCH3
I
OH

2. CH2=CH-CH2-O-CH2CH2OH

3. C6H5-CH2-C(CH3)3

4. (CH3)3C-CH2OH

Values:
a. 61.6, 71.6, 72.2, 117.2, 134.7
b. 29.5, 31.8, 50.2, 125.5, 127.5, 130.3, 139.8
c. 19.0, 31.7, 69.5
d. 18, 23.3, 24, 39, 68, 124, 132

2. Draw 1-ethoxy-3-iodo-2-isopropylbenzene

3. Name this compound using NORMAL names.

The other one has a Cl on the top a COOH one to the right and a Cl two to the left.

4. Draw products A and B of the following series of reactions.

Benzene + Br2/FeBr3 --> Product A
Product A + (CH3CH2CH2CH2)2 CuLi ---> Product B

5. Show a completely different, good way to make product B above, starting from benzene. The method should not involve halogenations of the ring.